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Preparation method and application of tetraphenyl ethylene derivative containing imidazole ring structure

A technology of tetraphenylethylene and imidazole rings, applied in the preparation and application in cell staining, the synthesis and application of TPE imidazole ring fluorescent dyes, can solve the low sensitivity of fluorescent sensing systems and restrict the application and development of fluorescent dyes and other problems, to achieve the effects of simple post-treatment, simple synthesis method, and mild reaction conditions

Active Publication Date: 2020-11-27
CHINA THREE GORGES UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because such molecules can only emit light in good solvents and low concentrations, the sensitivity of the fluorescent sensing system is low, and fluorescent materials often exist in the form of solid and aggregated states in applications, and the ACQ effect greatly restricts the use of such fluorescent dyes. Practical Application and Development

Method used

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  • Preparation method and application of tetraphenyl ethylene derivative containing imidazole ring structure
  • Preparation method and application of tetraphenyl ethylene derivative containing imidazole ring structure
  • Preparation method and application of tetraphenyl ethylene derivative containing imidazole ring structure

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Experimental program
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Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of compound 1

[0036] Weigh 4-(1,2,2-triphenylvinyl)benzaldehyde (53.8mg, 0.15mmol), ammonium acetate (57.9mg, 0.75mmol) and 1,10-phenanthroline-5,6-di The ketone (37.9mg, 0.18mmol) was dissolved in 5ml of acetic acid and refluxed at 110°C for 3.5h. After the reaction was completed, the reaction solution was poured into 20 mL of water, and an orange solid was precipitated. After filtering, washing with water and drying, an orange solid was obtained, namely dye 1, with a yield of 58.9%.

Embodiment 2

[0037] Embodiment 2: the synthesis of compound 2

[0038] Weigh 4-(1,2,2-triphenylvinyl)benzaldehyde (54.1mg, 0.15mmol), ammonium acetate (57.8mg, 0.75mmol) and 9,10-phenanthrenequinone (37.5mg, 0.18mmol) Dissolved in 5ml of acetic acid, reflux reaction at 110°C for 3.5h. After the reaction, the reaction solution was poured into 20 mL of water, and an orange solid was precipitated. After filtering, washing with water and drying, a light yellow solid was obtained, namely dye 2, with a yield of 78.4%.

Embodiment 3

[0039] Embodiment 3: the synthesis of compound 3

[0040] Weigh 4-(1,2,2-triphenylvinyl)benzaldehyde (72mg, 0.2mmol), ammonium acetate (77mg, 1mmol) and benzil (63mg, 0.3mmol) and dissolve in 5ml acetic acid, in Reflux reaction at 110°C for 3.5h. After the reaction, the reaction solution was poured into 20 mL of water, and a yellow solid was precipitated. After filtering, washing with water, and drying, a white solid was obtained, namely dye 3, with a yield of 50.5%.

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Abstract

The invention discloses a fluorescent dye with AIE properties and a preparation method thereof. The invention provides a synthesis method of a tetraphenyl ethylene (TPE) derivative fluorescent dye with a structure shown as a formula (I), wherein the substituent R is an aryl conjugated system. 4-(1, 2, 2-triphenylvinyl) benzaldehyde is used as a starting raw material and reacts with aryl diketone derivatives respectively to synthesize a series of imidazole ring-containing compounds, and the compounds have typical aggregation-induced emission (AIE) properties. The preparation method of the fluorescent dye is simple, the operation is simple and convenient, the cost is low, and the series of fluorescent dyes show strong solid fluorescence. The fluorescent dye can be applied to the fields of bioluminescence imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and specifically relates to the synthesis and application of a class of TPE imidazole ring fluorescent dyes, mainly including the preparation of the TPE imidazole ring fluorescent dyes and their application in cell staining. Background technique [0002] Organic fluorescent dye molecules, as an important part of fluorescent probes, are widely used in bioimaging, biomolecular labeling, environmental analysis, cell staining and clinical diagnosis, photochemical therapy, organic light-emitting diodes, etc. It is an indispensable and important tool in the fields of , environmental science, medicine and materials research. The design and synthesis of new fluorescent dyes and the development of various functional fluorescent dye molecules with practical value have become a research hotspot that has attracted much attention. [0003] At present, most traditional organic dyes emit strong fluoresc...

Claims

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Application Information

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IPC IPC(8): C07D233/58C07D233/64C07D235/02C07D401/14C07D471/14C09B57/00C09K11/06G01N21/64
CPCC07D233/58C07D233/64C07D235/02C07D401/14C07D471/14C09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1074G01N21/6428G01N21/6458
Inventor 郑开波陈慧李梦王丽红郑海峡
Owner CHINA THREE GORGES UNIV
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